ThoroughlyBadHat is being extraordinary
Your road trip sounds awesome. I hope you don’t mind me saying this, but you seem like a very interesting person. All of your goals seem to have deep personal meaning.
How to go on a road trip
It made me
rejuvenated 
"Everybody needs to do this at some point in their life."
How I did it: I flew from New York to Los Angeles, where I bought a car. Drove it to my hometown in Miami, FL., by taking the southern route (Route 66 for some part of it.) Went through 11 states in the South and stayed in Miami for a little while. Once I was done, I packed all my things from my mom's house and headed up to New York, where I took all of my things there out of storage and packed them into the back of my car. I gave my furniture to charity and just took what I could fit into the car. From there I took the northern route into San Francisco and down the Pacific Coast Highway to L.A. again. All in all, I visited 33 states, spending at least a day and night in each one with various friends I've made over the years who lived in each.
Lessons & tips: Invest in a good camera and a tripod. Also make sure you have an mp3 player with an auxiliary cable, and make an itinerary for places you want to see and when you plan on being at different places, but don't always follow it. Make your sub-trips less than four hours and make sure to meet up with old friends from work, school, childhood, etc., when ever you're passing through their state. It's worth it. Never stay in a hotel that costs more than $30 a night. If you can't find any, keep driving-- you will.
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